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Your Bad Date Stories 2014

Reader-submitted tales of some truly horrendous “romantic” encounters.

With dates like these, being single doesn’t seem so bad. Image via Shutterstock.

In honor of Valentine’s Day we asked you to share your worst date stories—and, like many of you who submitted, we got more than we bargained for. From a congressman’s son with a penchant for shirtless selfies to a new fiancée who finally showed her true colors, the characters in these stories will make you even more grateful for that special guy/girl/pint of Ben & Jerry’s in your life. If after reading these, you’re not put off of the idea of love for good, we hope to see you at our Singles Soiree tonight—you might get a great date out of it (or at least some material for next year’s roundup).

Culture Shock

I met a guy late night at a bar in DC, and we exchanged numbers. He texted me to meet up later that week for happy hour, and I agreed, because he was cute and dressed well. We ended up getting wings and beers at the Big Hunt, and it turned out he was a well-known Republican congressman’s son— so DC. We chatted for a bit, and his Southern charm really drew me in. I was warming to the guy when he stopped mid-conversation to tell me how nice my hair was. I had straightened it for the date, and admitted to him that it’s naturally curly. I joked, “I’ve got that Jew fro some days.” He looked perplexed. “Are you Jewish?” he inquired. Caught off guard by the abruptness of his question, I stammered, “Uhh, yes, well, half. My mom isn’t, but my dad is.” He continued to stare at me. I swear he was looking for the horns. After a few moments he just gave a little shrug and said, “Hmm, I’m not sure I’ve ever met a Jew before.”I sat there on the bar stool, stunned and utterly weirded out. Whether I was the first Jewish person he’d met or just the first Jewish person he realized he’d met, I was done with the date. There could be no future with someone so utterly moronic. I gave him a half smile, set $20 on the counter, and walked home.

In the days that followed, he sent a few texts alerting me to the fact that he was “headed out of town for a bit,” to which I did not respond. About two weeks later, I received a text out of nowhere from the guy with just a photo of him, shirtless, on a tractor. He was wearing Army fatigue bottoms and proudly holding a rifle in the air in what I can only assume he believed to be a manly, patriotic gesture.

What the WHAT?

Second Time’s the Charm

Had a good date with a Polish guy I met on Tinder, and a week after I went to a bar with some friends and saw him with another (Tinder?) girl, doing the SAME THINGS he did with me when we went out. Zero creativity! He pretended he didn’t see me and left the bar. As soon as he left, I texted: “It was great seeing you tonight :)” Obviously, no response. Maybe this is not a bad story, but I thought it was really funny!

Oh, Baby

It was a second date with a guy I met online; I was 26 and he was 25. We’re enjoying a nice meal on an outside patio of a restaurant when he says to me, “If a crazy girl comes up and attacks you, don’t worry—it’s just my ex-girlfriend.” I thought he was joking but wasn’t entirely sure. In hindsight, I should have taken that cue to leave immediately. He then starts talking about his niece and nephew and how much he loves them … and how jealous he is of his sister for having two children. He then announces has baby fever and wants a baby really bad. Thinking it’s definitely a joke this time—because what 25-year-old man says that?—I laugh. He asks, “Why are you laughing? Don’t you have baby fever, too?” Now I realize he is not joking. I start to panic, thinking I’m sitting across from a man who just needs my eggs and uterus before dessert arrives. I indicate I’d probably like to have kids, but in a few years. He asks, “Exactly how old do you want to be?” I say, “I don’t know, my early 30s?” To which he replies, “Aren’t you afraid you’ll be dried up by then?” We then have an awkward debate regarding women’s reproduction. At that point, baby fever dude and I are officially on the date from hell. I excuse myself to go to the ladies’ room, where I can’t stop laughing. Before departing I make several anti-baby comments to prevent him from calling me again—which, luckily, was successful.


Without going into too much detail (thus revealing yet another layer of my incredible stupidity), let’s just say there were multiple red flags waving before this date even happened. I agreed to meet this guy by his apartment in Fairfax, after which we’d head to a bar. He was insistent that we met up near his house because he lived so close to the bars. It wasn’t until he walked toward my car—a Virginia Tech drawstring backpack confidently slung over his shoulders—that I realized this was simply a ploy to get me to drive. It quickly became apparent that he was not well-versed in the art of conversation. In fact, I’m not sure he’d ever actually had one before. Twenty minutes and a million one-word answers later, we were in Reston. He’d tricked me into driving him to Reston. We walked into a sports bar and ordered drinks, and then he immediately disappeared for ten minutes. I sat nervously drinking my beer wondering whether he would come back or whether he had really just needed a ride. His return didn’t bring much relief, though, as he continued to have the personality and conversation skills of a turd. After one drink he suggested we get out of there. “Where? Another bar?” “Sure.” We did not go to another bar. Instead, he directed me through a residential area. Turn here, turn there. He’s from Reston, I thought. He knows his way around. The last turn was onto a rocky path that led up to a field located next to a power station. This is when my fight-or-flight response finally kicked in. “What is this? Why are we here? I thought we were going to a bar!”

*pop* “Do you like Bud Light or Miller Lite?” He had opened a can of beer in my car. A can of beer he pulled from his Virginia Tech drawstring backpack. “I thought we could sit here and drink,” he said. “I used to come here in high school all the time.” I wanted to leave, but now I had this six-foot-two stranger in my car with an open container. So I sat there expressing my discomfort over and over while he told me how he had gotten used to bringing beer to the bar in college because beer was so expensive. (I’d like to add that prior to this he had told me he made six figures, and I paid for my own $5 Blue Moon.) It suddenly occurred to me that this is where he disappeared to earlier when we arrived at the bar. He had been in the bathroom, pulling cans out of his bag o’ beer and chugging them in a stall like—well, like a high-schooler.

He also asked me the following questions: Are you afraid of power lines? How long was your last relationship? What was your last boyfriend like? What things are you looking for in a man? Why are you so nervous?

As soon as the last drop of Bud Light touched his lips I turned on my car and said we were leaving. He wanted to head home. I was more than okay with that. The conversation turned to boxing, by which I mean, unprompted, he started talking about intricate details of boxing technique and various fighters. I cared about none of this, but I was happy not to have been murdered in that field. We turned in to his complex, and I stopped in front of his house. He didn’t get out. “Um, is this good?” “Oh, I thought you were gonna pull in.” “ … … Nope.”

In conclusion, this boy made me drive, didn’t pay for my drink, tricked me into driving to a field, where he offered me lukewarm, bottom-shelf beer from a drawstring backpack, and STILL thought he was going to get lucky.

What, No Breadsticks?

Last March, I had finished a ten-week cross-fit training course at a local gym. The trainer had always been very friendly, and at the end of the course, he asked if I wanted to go out to dinner to celebrate. We made plans for him to pick me up from my house that Friday at 7. He showed up around 8 completely hammered and asked if he could come in for some water before dinner. I let him in, and he made himself comfortable on the couch while I went into the kitchen to grab a glass of water. Unbeknownst to me, in the one minute I was gone, he ordered an anchovy, sausage, and pineapple pizza for delivery to my house. I was still trying to get over the fact that this guy showed up drunk to pick me up for a dinner date but decided to just embrace the evening, since I had spent three nights a week for the past ten weeks sweating in front of this guy, which made me feel like we had some sort of bond.

Within 15 minutes, the pizza guy came. My trainer explained he ordered the pizza so we could have dinner in, but didn’t have any cash on him. I begrudgingly paid for this disgusting pizza. Then I went upstairs to call my friend to tell her about my awesome Friday night, and when I came downstairs, half the pizza was gone and the guy was passed out on my couch. I could not wake him up, so I put a Post-it note on his head to please let himself out when he woke up, and called it a night. The next morning, he was STILL on my couch. He apologized for the previous evening, saying he went on a really bad blind date right before he came over and got really drunk. He then asked if I would be up for getting brunch. I think I’ll pass. I also think I’ll find a new gym.

Close Encounters

A few months ago, I met a cute girl at a local coffee shop. After talking for a while, we decided to exchange numbers and grab drinks later in the week. We had only agreed to drinks, which I’ve found to be a pretty solid first-date rule, yet when we met at the bar she mentioned that she was hungry and began perusing the food menu. Always looking to avoid an awkward situation, I decided to go with it, and we ended up having a fairly good time over dinner. Nevertheless, I didn’t feel like we had much chemistry and decided not to pursue it beyond the first date. Flash-forward a few weeks. I’m sitting at the same table in the same coffee shop on another weekend afternoon. There is an open seat to my left, and next to that was an attractive girl working on her computer. There are also a good number of open seats throughout the room, all much more accessible and convenient than the one next to me. I look up from my computer when I notice someone walk into the room from the coffee bar; it’s the girl I had met a few weeks earlier. Being the mature guy that I am, I instantly bury my head in my computer screen and hope she doesn’t notice me. Apparently, she had already seen me and taken note of the vacant seat next to me. She navigates herself around power cords, chairs, the edge of the table (which is in a corner), and the girl to my left, and then wedges herself in the seat between us. The other girl almost immediately begins shutting down her computer and leaves. Again, with the maturity expected of a 16-year-old, I rotate my body away from her slightly and try to avoid making eye contact. After about five minutes, though, I can’t handle the unbelievable awkwardness of the situation any longer and decide to pack up and leave. As I’m doing so, she turns to me and, feigning surprise, says, “Oh, hey!” I manage a few minutes of uncomfortable small talk, settle on an excuse for why I had to leave, and then head to the nearest place I could grab a beer. Needless to say, I have not been frequenting that coffee shop lately.

A Giant Problem

Last Saturday my girlfriend of 15 months and I had dinner at La Ferme in Chevy Chase, Maryland. It was a very special occasion: not only her birthday and Valentine’s day, but also the night I offered her a ring and asked her to marry me. She said yes; dinner was wonderful. Afterward we went dancing at 9:30 Club’s back bar and slept at her brother’s place in Columbia Heights. It was a night to remember. The next day, we walked to Giant for some breakfast groceries. We picked out what we needed for breakfast. Then we got into the wrong self-check-out lane. The guy checking out in front of us must have been taking too long for my new fiancée, because she called him an $&@@&! The next self-checkout lane looked to be clearing faster; however, a mysterious basket full of groceries had been left on the ground unattended. I tapped the shoulder of the gentleman nearest the basket to ask if the groceries belonged to him, to which he said no, so I slid the obstruction out of our way and we moved into the new lane. That was when the stranger arrived. She said something like, “Excuse me, did you guys see my basket?,” to which my fiancée replied, “We moved it the $&@$& out of our way.” The stranger gasped then expressed to her friend (via Bluetooth headset) her opinions of my fiancée’s behavior in no uncertain terms.

What seemed like an eternity later, we finally made it outside into the cool open air. I mistakenly thought the strange experience was behind us. That was, until the woman I had asked to marry me less than 24 hours ago began cursing and belittling me for not “defending her” inside the grocery store. She then made it clear she no longer wanted my company when she told me to hand over the grocery bags I was carrying, as I couldn’t find my way back to her brother’s house anyway. I dropped the bags, told her where she could put them, found my car, and drove myself home. We were engaged before dinner and broke up before breakfast.

“Special” Occasions

Bad date stories? Oh, I have a few The first: I was probably 18 or so, and was on a blind date with a friend. Turns out the guys thought a perfect date was to hang out on the loading dock where they worked and drink beer. The trouble is, it was prom night, and the cops were out in force. My date was arrested for possession of alcohol as a minor and, I believe, driving while intoxicated, despite being parked—because it was his car, and the trunk was packed with alcohol. The cops made the guys pour it all out, and my girlfriend and I luckily weren’t charged with anything but had to walk back to our cars, maybe a mile or two. I haven’t been on a blind date since. Oh, and in case you’re curious, no idea whatever happened with the guys.

The other: I met a guy in New Orleans on New Year’s Eve. We really hit it off, and turned out we were both from Virginia: He was living in Norfolk, and I was at school in Blacksburg. We talked and e-mailed, and then he visited the weekend before Valentine’s Day, which was, like, Tuesday. He sent flowers before he arrived, and we had a really wonderful weekend. He stayed until the latest possible moment to get back to work. Then on Valentine’s Day, I got an e-mail: “Sorry, had a great weekend, but I’m getting back together with my girlfriend. We can still be friends.” No thanks, I told him, I have enough friends. There are a couple more, but I’ll leave it at those—unless I should share about the lying/cheating guy I dated for more than a year, whom I thought I was still dating but who married—yes, married—his ex without actually breaking up with me, and I found out from a friend of his. Yeah, I know how to pick ’em.

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